I'm going to assume that you don't need "low cost" as one of the options as you mention it is for primarily dev work
The "trick" in my experience to to use a connector sytem where the male pins are on the pcb and the female ones on the harness, and then use an adaptor harness to another connector that suits your programmer or programming hardware interface etc
This means the pins of the connector half which is soldered to the pcb itself, and therefore annoying/difficult to replace, don't wear out much (solid pins are tough and resillient) and the interface harness can be connected to the programmer once and left connected, and then really the bit that wears out are the female contacts in the socket on the end of that adaptpr harness, as these are the ones being mated/unmated regularily and getting bent & abused etc.
I use Molex Picoblade SMC series connectors, usually in 8 way format, and the right angle and straight version share the same pcb footprint, so you can install which ever works best to have the programming connector coming off the board at right angles or horizontally. The connector has a strong latch so it's reliable enough for bench work, but not so strong you can't pull it out before you damage the halfs or peal the connector assy off the pcb. They are pretty cheap, and with the 8 way version, i can include debugging coms (UART etc) and have a standard pin out for all projects. This 1.25mm pitch means even 8 pin in a row is stil pretty compact
When the female contacts in the adaptor harness finally get too loose and un-reliable, i just bin that bit and make another adaptor harness to suit what ever the programmer requires (JTAG 2x10 etc) depending on what micro/programmer is being used.
https://www.molex.com/en-us/part-list/53261?taxonomyPathValueLast=PCB%20Headers%20and%20Receptacles